


Penny For Your Thoughts? (Dean Winchester x Reader)

by Sarcastic_Writer



Series: Supernatural Reader Inserts [4]
Category: Supernatural
Genre: Episode: s09e07 Bad Boys, F/M, Gender-Neutral Pronouns, I'm Bad At Summaries, Implied/Referenced Child Abuse, John Winchester's A+ Parenting, M/M, Other, Other Additional Tags to Be Added, Teenagers
Language: English
Status: In-Progress
Published: 2019-01-05
Updated: 2019-02-11
Packaged: 2019-10-04 20:31:39
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 2,010
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17311391
Author URL: https://archiveofourown.org/users/Sarcastic_Writer/pseuds/Sarcastic_Writer
Summary: You meet Dean at Sonny's, but you aren't just another kid. You're Sonny's kid. And you become interested in Dean. So, this is your story.





	1. Part 1

You peeked around the corner of the doorway as Deputy Billy sat the boy down on the couch. Sonny looked him up and down and you watched as the deputy revealed his black-eye, the black-eye the boy seemed proud of. Sonny bids the deputy goodbye and you stifle a laugh when you realize he left with the keys. Again. Sonny realized this and told the boy, whose face dropped.

“(Y/N), could you go grab my lockpick?” Sonny calls out to you and you jump. You had no idea he knew you were watching. The boy seemed surprised as well, not knowing you were watching him. You threw him a small smile before going into the kitchen and opening the drawer where Sonny kept his lockpick. When you went back to the living room you heard Sonny speaking, “That’s (Y/N), I adopted them about 10 years ago. They were the first kid I took in.”

You decided to enter the room, throwing Sonny his lockpick, “And it’s a miracle I’m the only one who was adopted.”

Sonny nodded in agreement as he opened the boy’s cuffs, “I’ve been damn close though.”

“As he said, I’m (Y/N),” you introduced yourself as the boy rubbed his wrists. He looked up at you distrustfully before he returned the greeting.

“Dean.”

You decided to cut to the chase, “So, why’d you steal that food?”

“(Y/N)!” Sonny said, immediately reprimanding you. “Not everyone is as open and willing to talk like you.”

You looked up at Sonny with a fake glare. “You calling me chatty?”

` Sonny nodded, “That’s exactly what I’m calling you.”

You shrugged, he was right after all. You turned back to Dean and gave him an apologetic smile. “You don’t have to say, by the way. I just like to ask.”

Dean nodded slowly and you heard Sonny sigh. You turned to face him and he gave you a smile and said, “Why don’t you go show Dean where he’ll be stayin’ kid? I’ve gotta do a bit of work before we go out.”

You nodded and held a hand out to Dean. He didn’t take it., only looked at it warily. You sighed in annoyance and said, “Come on, take it. I don’t bite.”

Ignoring Sonny’s reprimand you quickly pulled the boy out of the house once he took your hand. It was silent as you walked towards the bunk-building, but you could tell something was on Dean’s mind.

“Penny for your thoughts?” you asked him, fishing a penny out of your pocket. You held it up to him and he looked at him, amused. He was silent again, seeming to be fighting with himself; something he did a lot. Or, at least, something he did a lot around you.

Slowly he reached out and grabbed the penny. You grinned widely and waited for him to gather his thoughts. After a moment, he spoke. “Of all the kids Sonny’s had, why only you?”

You were shocked, you honestly didn’t expect that one. Fortunately, you were saved from answering as you finally reached the building. You opened the door quietly.

When you entered the room you stopped in the doorway and narrowed your eyes when you saw one of the boys (Dennis) sitting on his bed reading a comic. Evidently, he didn’t notice your entrance so you motioned for Dean to be quiet. You snuck up on Dennis and as you leaned against his bed frame you said, “Whatcha doing there Dennis?”

Dennis jumped and dropped his comic he looked up at you with a sheepish smile and replied, “Um, just gettin’ back, um, to work.”

You nodded with an ‘mhm’ as Dennis shot off his bed, quickly greeted Dean and left to do his chores. Dean looked at you, impressed. You motioned to the bed next to Dennis’ and said, “This one’s all yours. Any questions?”

_ Just not the one you already asked,  _ you pleaded in your mind. Dean, somehow, understood. Mind-reader probably.

So, Dean looked around as he walked over to his new bed. He sat down on it and looked at you curiously as he asked, “Do all the boys listen to you.”

You shrugged with a devilish smirk. “If they’re smart. There are some benefits to being Sonny’s kid. Legally at least.”

Dean nodded in understanding before asking another question, “What was Sonny talkin’ ‘bout when he said ‘before we go out’? You two have some bi-weekly dinner or something?

You shrugged again, not wanting to spoil the surprise and said, “Or something.”

Dean groaned at your answer, clearly wanting a solid one. But where was the fun in that? You watch Dean as he went silent, observing the room from his new point. You couldn’t help but smile. You could tell he was going to fit in fine.

_ ~Time Skip~ _

You were lounging on Dean’s bed as you waited for his return from the lunch Sonny took him two. You smiled at the memory of the shock on Dean’s face when he found out what the ‘something’ was. It seemed like no one had ever taken him out to eat just because, though, you’d be willing to bet most of the boys hadn’t. 

You were absorbed in your thoughts as Dean walked over to his bed. He smirked a bit as he noticed you. He really wasn’t sure what he had been expecting when he first saw you; some teen that had been watching him? No thanks. But you were actually very refreshing. After years of his father’s strict and emotionless ways, Dean had forgotten what it was like to know that someone was willing to listen to his problems. Well, Sammy probably was, but there was no way in hell Dean was dumping his shit on his baby brother. Never.

You on the other hand…

Well, Dean mused as you shot up with a grin and question flying out of your mouth when you noticed him, maybe he’d give you a shot.


	2. Part 2

 

You had tried your best, you really had. But, are you really to blame? It’s not your fault Dean is shit at playing the guitar. Sure, the boy could do field work like no one’s business, but God forbid he could sit still long enough for you to actually teach him how to improve.

Dean had been staying at Sonny’s for almost two months and you’ve actually managed to pry out information about his life, albeit very little. Most that his mom died when he was young, he had a baby brother Sam, and his dad carted them around the country for his ‘job’. There was a silent agreement between the two of you to not talk about why you were at Sonny’s.

Since you were Sonny’s kid, not one of the boys staying here, you didn’t technically have to do work. But you enjoyed hanging out with the boys as they worked, playing the guitar and helping out when needed. When Dean had learned you could play the guitar he was surprised, but ultimately brushed it off. That led to you confronting him where he shrugged and told you it couldn’t be that hard to do. Which lead to you trying to teach him to play. Needless to say, he is still too stubborn to admit he was wrong.

This all lead to where you are now, sitting underneath a tree in Sonny’s backyard on Dean’s break from work with two guitars (one is your’s and the other is an extra). Dean’s brow was furred as he looked at the ‘How To Play Guitar For Idiots’, a book he was slightly offended at when you first handed it to him. But now he didn’t seem to care as he tried to get his fingers to stay in the position he wants for the first note of the simple melody presented in the book. 

You chuckled as you watched him, arms rested on your guitar. He was so cute, brow furred, eyes squinted, and tongue barely poking out as he plucked the first note. It was a bit off, but he looked so proud of himself you couldn’t bring yourself to tell him. Instead, you played the same note followed by the next note he needed to play. Dean tried to copy you, but his fingers slipped and he sighed in annoyance.

You chuckled at him and he glared at you playfully. “At least you’re trying.”

“Ya’know, usually when I do stuff I’m good at it,” Dean said as he put his guitar down and pulled yours from your lap. He laid down and rested his head on your lap, frowning up at you.

“You can’t be good at everything De,” You placated as you ran your fingers through his hair. He hummed contentedly and let his eyes shut. You allowed yourself a moment to look at him. When his eyes were closed and he was relaxed he seemed to de-age, looking like an actual 16 year-old. He had a small grin on his face and all stress lines seemed to disappear. 

“I’ve got a meet tomorrow,” Dean mumbled, not opening his eyes. “Wanna go to Cus’s Place after?”

You hummed, jokingly considering. “I don’t know De, I’m usually pretty tired after a meet.” Dean opened his eyes and glared playfully at you as you continued, moving his head so you could lie down. “What if I just want to go home and sleep?”

Dean snorted and sat up on his elbows as you stayed sprawled out on the grass. He poked your side as you flinched. “Well, I know  _ that’s  _ bull. You always want to go to Cus’s.”

You shrugged. “It’s true. Besides, when would I ever break our tradition?”

Dean chuckled and laid down next to you. It was quiet for a moment as the two of you watched the clouds, listening to the distance voices of the other boys running around. You were enjoying the peace while Dean was still trying to wrap his head around it. He had a tradition. He could barely remember the last time he had one of those. He liked it.

“Ya’know, semi-formal is soon,” you mumbled while turning to look at Dean. He turned to you with a raised eyebrow. “You wanna go with me?”

“Aren’t I supposed to ask you?” Dean teased. You threw an arm across your face and mumbled a ‘fuck you’ while Dean laughed. You felt a poke on your arm and you lifted it to see Dean leaning over you with a smile. “I’ve never been to a school dance.”

You sat up with a confused expression and Dean followed. “Really?” you asked, having a hard time believing it.

Dean shrugged casually, but he was kind of uncomfortable, not used to sharing much about himself. “I’ve never really been at a school long enough.”

You suddenly popped up and grabbed Dean to pull him with you. He laughed as he followed you to the house. “Where are we going?”

You stopped and turned to him with an excited smile. “To get you a suit of course! Sonny’ll be more than happy to get you one!”

You turned back around so you didn’t see Dean shake his head fondly. He still had a hard time believing that you really cared about him, he was just waiting for the moment everything would be pulled away from him. 

Dean stopped and you turned to him with a confused expression. You opened your mouth to ask him what was wrong when Dean quickly leaned him and kissed you. He pulled back with a smirk and you gaped at him for a second. You pouted at him.

“There are other ways to get me to shut up,” you told him. He shrugged, still smirking. You rolled your eyes at him and kissed him quickly before pulling him along again, talking his ear off about how much he was going to love the dance.

Yeah, Dean really hoped whatever was out there gave him more time before they fucked up his life. Again.

**Notes for the Chapter:**

> There will be at least 2 more chapters to this btw.


End file.
